An Alternative to ‘propylene/Leonard linker’ for Studying Arene Interactions in Flexible Pyrazolo[3,4-d]pyrimidine Core Based Models Both at Molecular and Supramolecular Levels

Avasthi, Kamlakar and Ansari, Amantullah and Kant, Ruchir and Maulik, Prakas R and Ravikumar, Krishnan and Chattopadhyay, Partha and Adhikary, Nirmal D (2011) An Alternative to ‘propylene/Leonard linker’ for Studying Arene Interactions in Flexible Pyrazolo[3,4-d]pyrimidine Core Based Models Both at Molecular and Supramolecular Levels. Cryst Eng Comm, 13 (6). pp. 2039-2046.

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    Abstract

    An alternative C-3 linker to ‘propylene/Leonard linker’ is proposed for studying arene interactions in face-to-face (offset) mode. The two new flexible symmetrical compounds with an electron deficient pyrazolo[3,4-d]pyrimidine core and biologically important isomeric purine systems and one dissymmetrical compound with a pyrazolo[3,4-d]pyrimidine core and electron-rich carbazole residue at the termini of the new linker show folding due to intramolecular p–p interactions by both 1H NMR in solution and X-ray crystallography in the solid state. Surprisingly, the replacement of the 4- methylsulfanyl group of the dissymmetrical compound by an electron donating methoxy group shows open conformation in the solid state by X-ray crystallography. The fifth symmetrical compound with an electron-rich carbazole residue at the termini of new linker, however, shows the normally expected open conformation.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/59
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Mr Shyamal Nath
    Date Deposited: 28 Sep 2011 19:41
    Last Modified: 03 Jan 2012 16:00
    Official URL: http://dx.doi.org/10.1039/C0CE00336K
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